


Milking Time

by BottomDean67



Category: Supernatural
Genre: Alpha Sam Winchester, Alpha/Beta/Omega Dynamics, Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Chastity Device, Cock Cages, Dry Orgasm, Fucking Machines, Gags, Happy Ending, M/M, Omega Dean Winchester, Orgasm Delay/Denial, Prostate Milking, Roleplay, Sounding, Top Sam Winchester
Language: English
Status: Completed
Published: 2019-09-02
Updated: 2019-09-02
Packaged: 2020-10-05 18:06:57
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 832
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20493023
Author URL: https://archiveofourown.org/users/BottomDean67/pseuds/BottomDean67
Summary: When Sam became Dean's Alpha, he knew Sam would have some strict rules for him. His brother's love for watching him come dry was not what he was expecting.





	Milking Time

“Omega. I’m home!” called Sam. Dean sighed from where he waited in the playroom upstairs, bent over the breeding bench obediently. His back was to to the door but he heard when Sam came in. “You have the most gorgeous ass, Omega.”

“Thank you, Alpha,” said Dean quietly. 

“Someone doesn’t seem excited for their orgasm,” he said. “It’s been two weeks after all.”

Dean remained silent, a heavy hand pressing down on the back of his neck.

“Answer me, bitch.”

“I’m excited, Alpha,” said Dean, Sam squeezing him hard enough to leave bruises. “Please milk me, Alpha.”

“I don’t think I’m in the mood to help out such an ungrateful Omega,” he said, quickly securing Dean in the restraints. “The machine can milk you tonight.”

Dean wanted to groan. The fucking machine had a knobby, ten inch dildo that rubbed Dean’s prostate mercilessly. He knew better than to say anything though.

Sam slapped Dean’s ass a few times before he pulled out his chastity plug and lubed on the dildo, sliding it in where he wanted before he turned it on.

“Alpha?” asked Dean wearily, Sam walking in front of him with a ball gag in his hand. “I’m wearing a sound.”

“You better hope I’ve forgiven you then by the time you start dripping milk,” said Sam. Dean went wide eyed and Sam slipped the gag in mouth, Dean already trying to beg him to take it out. Sam hummed and walked to Dean’s side, kneeling down to look at his caged cock and large balls. “Been two weeks since we milked you. Starting tomorrow, we’re putting you on three pills a day versus the two and you’ll be milked once a month to get you extra full. I hope this will teach you about being ungrateful for your orgasm. Most Omegas don’t get to come at all.”

Dean dropped his head. Sam was pissed. He’d threatened it before but they both knew it was too dangerous to let Dean go that long without a release. He’d have some serious making up to do but he’d do it. His balls already killed him. He wouldn’t be able to walk if he was forced to endure even more.

“Be good,” said Sam, patting Dean’s ass as he left.

The machine kicked up it’s speed and Dean could feel the dildo rubbing him. He tensed his body, trying to force back the milking, trying to keep it inside and not head into his poor trapped cock.

Twenty minutes later he was trembling, covered in sweat and tears when the door opened. Sam patiently walked around in front of Dean, grabbing his chin when Dean didn’t dare look up. 

Sam was smiling though and gave Dean a rare sign of affection when he ran his hand through his hair.

“You can be such a good boy when you try. My good boy. Now I want you to trust me. It’ll hurt but I want you to try for me. If you’re a good boy, we’ll go back to one pill a day and weekly milkings,” he said. “Do you want that Dean?”

Dean shook his head even before he heard his rarely spoken name used, Sam kissing his forehead. 

“Let go. I want to see. Let go, Dean.”

Dean forced himself to unclench his body.

He shouted so hard when the cum tried to leave him but was trapped in his cock, that he passed out.

  
  


_“Nhn,”_ groaned Dean as he woke up to Sam stroking his now free cock. Dean hissed and blinked open his eyes, Sam moving his hand harder and faster until Dean was crying from the oversensitive touch, his whole body tensing as he came dry.

“Good boy,” said Sam, Dean slumping against the bench, Sam reattaching his cockcage without the sound and putting in the plug before he untied Dean. “What do we say?”

“Thank you for the milking and orgasm, Alpha,” said Dean as he sat up, whole body still trembling as he tried to get his bearings.

“You’re very welcome, Omega. Now please go make dinner for us,” said Sam. Dean nodded as he stood, moving to leave when Sam grunted. “Forgetting something?”

Dean turned around and looked down at the floor, turning back confused. 

“What?” asked Dean. Sam smiled though and gave Dean a hug.

“I think we’re done with the rough Alpha scene, De,” laughed Sam. “A month was a long time.”

“Mmm,” said Dean, dropping his head against Sam’s shoulder. 

“Okay,” said Sam, picking Dean up. “You get out of that stuff and cleaned up in the shower and I’ll make us some dinner. How’s that sound?”

“Yummy,” said Dean. “Thanks for trying it Sammy.”

“That was tamer than half the shit we’ve done. I ever actually act like that you have full permission to kick my ass,” said Sam.

“You wouldn’t,” said Dean, nuzzling into his neck. “Shower with me. Please?”

“Alright. Then you’re getting the best aftercare session you’ve ever seen, Dean.”  
  



End file.
